Gleason was both an observer and a contributor to what is sometimes termed the San Francisco Renaissance, the era of increased cultural vitality in that city which began in the mid-1950s and fully bloomed in the mid-to-late 1960s. In the later 1960s, Gleason was a widely respected commentator and he chose to write supportively of the better cut of the Bay Area rock bands, such as Jefferson Airplane and the Grateful Dead. However, Gleason was sometimes criticized for minimizing the importance of or simply ignoring acts from Los Angeles. But others judged that he was making a valid distinction between works of creative vitality and music business product. In any case, Gleason was a key contributor to the growth and range of San Francisco region's vibrant music scene of the 1960s and after.

Gleason was a contributing editor to Ramparts, a prominent leftist magazine based in San Francisco, but quit after editor Warren Hinckle criticized the city's growing hippie population. With Jann Wenner, another Ramparts staffer, Gleason founded the bi-weekly music magazine, Rolling Stone, to which he contributed until his death in 1975. For ten years, he also wrote syndicated weekly columns on jazz and pop music, which ran in the New York Post and many other papers throughout the US and Europe. For twelve years, he was an associate editor and critic for the leading jazz publication, Down Beat.

Other films for television included a four-part series on the Monterey Jazz Festival, the first documentary for television on pop music, Anatomy of a Hit, and the hour-long programs on San Francisco rock, Go Ride the Music, A Night at the Family Dog, and West Pole.

Gleason's lasting legacy, however, would be his work with Rolling Stone. His name, alongside that of the late Hunter S. Thompson, still remains on the magazine's masthead today, more than three decades after his death.